Abstract
Fluorescent labelling of intracellular
organelles, proteins, or nucleic acids (NAs) is an essential way of studying
the structure and function of live cells. With their excellent photophysical
and biophysical properties, conjugated polymers (CPs) and conjugated polymer
nanoparticles (CPNs) are useful for labelling, sensing, and delivery of
biological substances. However, relatively large molecular weights and broad
molecular weight distributions of CP-based materials often limit their
intracellular applications in live cells. Due to a smaller hydrodynamic
volume, molecularly defined short conjugated oligomers (COs) appear to enter
cells by fast diffusion through the cell membranes, whereas CPs and CPNs are
most likely endocytosed and entrapped in endosomes or lysosomes. Despite their advantages,
there are few examples of COs being used for fluorescent labelling applications
in live cells.
To combine the advantages of conjugated
polymers (CPs) with more chromophores per molecule and conjugated oligomers
(COs) with monodispersed molecular weights and fast cellular entry, the
inventor has synthesized phenyleneethynylene macrocycles (PEMCs). The macrocycles
are prepared by using imine coupling between aldehyde end-capped
phenyleneethynylene (PE) trimer units and flexible diamines. For polycyclic
macrocycles, the amine can be triamines or tetraamines. Because the equilibrium
in the imine bond formation can be quantitatively shifted to thermodynamically favored
products, the target macrocycles can be obtained in high yields without
accompanying by-products.
Benefit
Can be obtained in high yields without accompanying byproductsExhibit fast cellular entry, RNA selectivity, and nontoxicity
Market Application
Visualization and imaging of cellular RNA using standard microscopy techniques
Publications
Moon et al. Phenyleneethynylene trimer-based rigid-flexible [2+2] macrocycles for
nucleic acid labelling in live cells. Chem. Commun., 2019,55, 5930-5933
Brochure
